US7638551B2ExpiredUtilityA1

Amino alcohol compounds or phosphonic acid derivatives thereof

77
Assignee: SANKYO COPriority: Jan 11, 2002Filed: Jan 9, 2007Granted: Dec 29, 2009
Est. expiryJan 11, 2022(expired)· nominal 20-yr term from priority
Inventors:Takahide NishiTakaichi ShimozatoFutoshi NaraShojiro Miyazaki
A61P 31/12A61P 9/10A61P 37/06A61P 7/06A61P 9/04A61P 9/06A61P 9/12A61P 43/00A61P 37/00A61P 9/00A61P 31/04A61P 33/00A61P 7/00A61P 35/02A61P 29/00A61P 25/14A61P 3/10A61P 25/28A61P 25/16A61P 25/24A61P 3/00A61P 25/00A61P 25/18A61P 17/00C07F 9/65515A61P 17/06A61P 1/04A61P 11/00C07F 9/655345A61P 11/06A61P 17/02A61P 21/00A61P 1/16A61P 1/00A61P 13/00C07D 207/335C07D 333/20A61P 17/04A61P 19/00A61P 11/08A61P 19/02C07D 307/52A61P 13/12C07F 9/572Y02P20/55
77
PatentIndex Score
2
Cited by
199
References
56
Claims

Abstract

A method for the prevention or treatment of an immunology-related disease, which is not rheumatoid arthritis or psoriasis, in a mammal in need thereof which involves administering to the mammal a pharmaceutically effective amount of a compound, a pharmacologically acceptable salt of the compound or a pharmacologically acceptable ester of the compound, wherein the compound is a compound having a formula (Ia): wherein R1 and R2 are each a hydrogen, R3 is hydrogen; R4 is C1-C2 alkyl; n is 2; X is -N-D, wherein D is hydrogen C1-C4 alkyl or phenyl; Y is ethylene, ethynylene, -CO-CH2 or phenylene; Z is ethylene or trimethylene; R5 is an unsubstituted C3-C10 cycloalkyl, an unsubstituted C6-C10 aryl, or a C3-C10 cycloalkyl or a C6-C10 aryl substituted with 1 to 3 substituents selected from the group consisting of halogen, lower alkyl, halogeno lower alkyl and lower alkoxy; and R6 and R7 are each hydrogen.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A method for the treatment of an immunology-related disease selected from the group consisting of Crohn's disease, ulcerative colitis, multiple sclerosis, atopic dermatitis, insulin dependent diabetes mellitus, glomerular nephritis and rejection of a transplanted organ or transplanted skin, in a mammal in need thereof which comprises administering to said mammal a pharmaceutically effective amount of a compound, a pharmacologically acceptable salt of the compound or a pharmacologically acceptable ester of the compound, wherein the compound is a compound having a formula (Ia) 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2  are each a hydrogen atom; 
         R 3  is a hydrogen atom; 
         R 4  is a C 1 -C 2  alkyl group; 
         n is 2; 
         X is ═N—D, wherein D is a hydrogen atom, a C 1 -C 4  alkyl group or a phenyl group; 
         Y is an ethylene group, an ethynylene group, a group of a formula CO—CH 2  or a phenylene group; 
         Z is an ethylene group or a trimethylene group; 
         R 5  is an unsubstituted C 3 -C 10  cycloalkyl group, an unsubstituted C 6 -C 10  aryl group, or a C 3 -C 10  cycloalkyl group or a C 6 -C 10  aryl group substituted with from 1 to 3 substituents selected from the group consisting of a halogen atom, a lower alkyl group, a halogeno lower alkyl group and a lower alkoxy group; and 
         R 6  and R 7  are each a hydrogen atom. 
       
     
     
       2. The method according to  claim 1 , wherein the mammal is a human. 
     
     
       3. The method according to  claim 2 , wherein, in the compound, R 4  is a methyl group, or a pharmacologically acceptable salt thereof. 
     
     
       4. The method according to  claim 3  or a pharmacologically acceptable salt thereof, wherein, in the compound, X is a group of a formula ═N—CH 3 , or a pharmacologically acceptable salt thereof. 
     
     
       5. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(3,4-dimethylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol, or a pharmacologically acceptable salt thereof. 
     
     
       6. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(3,5-dimethylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol, or a pharmacologically acceptable salt thereof. 
     
     
       7. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(3-trifluoromethylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol, or a pharmacologically acceptable salt thereof. 
     
     
       8. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(4-trifluoromethylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol. 
     
     
       9. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(4-methylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol. 
     
     
       10. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(4-methoxyphenyl)butanoyl]pyrrol-2-yl}butan-1-ol. 
     
     
       11. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(3-methylphenyl)butyl]pyrrol-2-yl}butan-1-ol. 
     
     
       12. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(3,4-dimethylphenyl)butyl]pyrrol-2-yl}butan-1-ol. 
     
     
       13. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(3,5-dimethylphenyl)butyl]pyrrol-2-yl}butan-1-ol. 
     
     
       14. The method according to  claim 2 , wherein said compound is 2-amino-2-methyl-4-{1-methyl-5-[4-(3-trifluoromethylphenyl)butyl]pyrrol-2-yl}butan-1-ol. 
     
     
       15. The method according to  claim 2 , wherein R 1 , R 2  and R 3  are each a hydrogen atom, R 4  is a methyl group, n is 2 and Y—Z—R 5  is (O—(CH 2 ) 3 -(4-F-phenyl). 
     
     
       16. The method according to  claim 2 , wherein the compound is selected from the group consisting of
 2-amino-2-methyl-4-{1-methyl-5-[4-(3,4-dimethylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(3,5-dimethylphenyl-)butanoyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(3-trifluoromethylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(4-trifluoromethylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(4-methylphenyl)butanoyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(4-methoxyphenyl)butanoyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(3-methylphenyl)butyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(3,4-dimethylphenyl)butyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(3,5-dimethylphenyl)butyl]pyrrol-2-yl}butan-1-ol; 
 2-amino-2-methyl-4-{1-methyl-5-[4-(3-trifluoromethylphenyl)butyl]pyrrol-2-yl}butan-1-ol; and 
 a compound of the formula (Ia), wherein R 1 , R 2  and R 3  are each a hydrogen atom, R 4  is a methyl group, n is 2 and Y—Z—R 5  is —CO—(CH 2 ) 3 -(4-F-phenyl), 
 or a pharmacologically acceptable salt thereof. 
 
     
     
       17. The method according to  claim 5 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       18. The method according to  claim 6 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       19. The method according to  claim 7 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       20. The method according to  claim 8 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       21. The method according to  claim 9 , wherein the configuration at the carbon atom to which the group of the formula NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       22. The method according to  claim 10 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       23. The method according to  claim 11 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       24. The method according to  claim 12 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       25. The method according to  claim 13 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       26. The method according to  claim 14 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       27. The method according to  claim 15 , wherein the configuration at the carbon atom to which the group of the formula —NR 1 R 2  attaches is the R configuration, or a pharmacologically acceptable salt thereof. 
     
     
       28. The method according to  claim 2 , wherein the disease is Crohn's disease or ulcerative colitis. 
     
     
       29. The method according to  claim 2 , wherein the disease is multiple sclerosis. 
     
     
       30. The method according to  claim 2 , wherein the disease is atopic dermatitis. 
     
     
       31. The method according to  claim 2 , wherein the disease is insulin dependent diabetes mellitus. 
     
     
       32. The method according to  claim 2 , wherein the disease is glomerular nephritis. 
     
     
       33. The method according to  claim 2 , wherein the disease is rejection of a transplanted organ or transplanted skin. 
     
     
       34. The method according to  claim 1 , wherein the disease is a host versus graft reaction. 
     
     
       35. The method of  claim 9 , wherein the disease is multiple sclerosis. 
     
     
       36. The method according to  claim 9 , wherein the disease is atopic dermatitis. 
     
     
       37. The method according to  claim 9 , wherein the disease is insulin dependent diabetes mellitus. 
     
     
       38. The method according to  claim 9 , wherein the disease is glomerular nephritis. 
     
     
       39. The method according to  claim 9 , wherein the disease is rejection of a transplanted organ or transplanted skin. 
     
     
       40. The method according to  claim 9 , wherein the disease is Crohn's disease or ulcerative colitis. 
     
     
       41. The method according to  claim 2 , wherein the disease is a host versus graft reaction. 
     
     
       42. The method according to  claim 9 , wherein the disease is a host versus graft reaction. 
     
     
       43. The method according to  claim 5 , wherein the disease is Crohn's disease or ulcerative colitis. 
     
     
       44. The method of  claim 5 , wherein the disease is multiple sclerosis. 
     
     
       45. The method according to  claim 5 , wherein the disease is atopic dermatitis. 
     
     
       46. The method according to  claim 5 , wherein the disease is insulin dependent diabetes mellitus. 
     
     
       47. The method according to  claim 5 , wherein the disease is glomerular nephritis. 
     
     
       48. The method according to  claim 5 , wherein the disease is rejection of a transplanted organ or transplanted skin. 
     
     
       49. The method according to  claim 5 , wherein the disease is a host versus graft reaction. 
     
     
       50. The method according to  claim 10 , wherein the disease is Crohn's disease or ulcerative colitis. 
     
     
       51. The method of  claim 10 , wherein the disease is multiple sclerosis. 
     
     
       52. The method according to  claim 10 , wherein the disease is atopic dermatitis. 
     
     
       53. The method according to  claim 10 , wherein the disease is insulin dependent diabetes mellitus. 
     
     
       54. The method according to  claim 10 , wherein the disease is glomerular nephritis. 
     
     
       55. The method according to  claim 10 , wherein the disease is rejection of a transplanted organ or transplanted skin. 
     
     
       56. The method according to  claim 10 , wherein the disease is a host versus graft reaction.

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